[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[Br:12]Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[Br:12][C:3]1[C:2]([OH:11])=[CH:1][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1An oven dried 1 L round bottom flask was charged with 5,6,7,8-tetrahydro-2-naphthol (4 g, 26.8 mmol) and CCl4 (536 mL). The solution was cooled to 0° C. with an ice bath for 30 minutes, followed by the slow addition of a solution of Br2 (4.28 g, 26.8 mmol) in CCl4 (27 mL). The reaction was stirred at 0° C. for 30 minutes then placed in the freezer at −10° C. for 18 hours. The reaction was then allowed to warm to ambient temperature. TLC shows the reaction complete. The reaction was concentrated in vacuo to give 6.16 g of an ivory laced with dark brown solid. The crude was purified in four batches by Biotage MPLC (120 g columns, 2.5% ethyl acetate). Purification gave 2.83 g (46%) of 1-bromo-5,6,7,8-tetrahydronaphthalen-2-ol as a white solid, 2.28 g (37%) of a mixed fractions (1-bromo-5,6,7,8-tetrahydronaphthalen-2-ol and 3-bromo-5,6,7,8-tetrahydronaphthalen-2-ol) and 0.56 g (9%) of 3-bromo-5,6,7,8-tetrahydronaphthalen-2-ol as a white solid.
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